Theoretical study on the reaction of hydrogen atoms with aniline

Marwan Batiha; Mohammednoor Altarawneh; Abdullah Alsofi; Mohammad Al-Harahsheh; Ibrahem Altarawneh; Saleh Alrawadieh

doi:10.1007/s00214-011-0940-x

Theoretical study on the reaction of hydrogen atoms with aniline

Marwan Batiha, Mohammednoor Altarawneh, Abdullah Alsofi, Mohammad Al-Harahsheh, Ibrahem Altarawneh, Saleh Alrawadieh

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

The reaction of aniline with hydrogen atom is investigated herein using the hybrid meta-DFT functional of BB1 K. Hydrogen atom is found to preferentially add at an ortho position. However, the fate of the o-(C₆H₅NH₂)H adduct is found to be solely the deactivation of the initial addition channel. The rate constant for the abstraction channel (C₆H₅NH₂ + H → C₆H₅NH + H₂) is fitted by the expression 1.10 × 10^-11 exp(-4,200/T) cm³ molecule^-1 s^-1. Our calculated rate constant for the abstraction channel agrees very well with the available experimental measurements. Satisfactory agreement is found between calculated and experimental measurements for the displacement channel (C₆H₅NH₂ + H → C₆H₆ + NH₂). Our detailed analysis for the corresponding displacements in toluene and phenol suggests that the three systems exhibit similar behavior with regard to the relative importance of abstraction and displacement channels.

Original language	English
Pages (from-to)	823-832
Number of pages	10
Journal	Theoretical Chemistry Accounts
Volume	129
Issue number	6
DOIs	https://doi.org/10.1007/s00214-011-0940-x
Publication status	Published - Aug 2011
Externally published	Yes

Keywords

Abstraction vs. displacement
Aniline
H atoms
Hybrid meta-DFT
Reaction rate constant

ASJC Scopus subject areas

Physical and Theoretical Chemistry

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10.1007/s00214-011-0940-x

Cite this

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title = "Theoretical study on the reaction of hydrogen atoms with aniline",

abstract = "The reaction of aniline with hydrogen atom is investigated herein using the hybrid meta-DFT functional of BB1 K. Hydrogen atom is found to preferentially add at an ortho position. However, the fate of the o-(C6H5NH2)H adduct is found to be solely the deactivation of the initial addition channel. The rate constant for the abstraction channel (C6H5NH2 + H → C6H5NH + H2) is fitted by the expression 1.10 × 10-11 exp(-4,200/T) cm3 molecule-1 s-1. Our calculated rate constant for the abstraction channel agrees very well with the available experimental measurements. Satisfactory agreement is found between calculated and experimental measurements for the displacement channel (C6H5NH2 + H → C6H6 + NH2). Our detailed analysis for the corresponding displacements in toluene and phenol suggests that the three systems exhibit similar behavior with regard to the relative importance of abstraction and displacement channels.",

keywords = "Abstraction vs. displacement, Aniline, H atoms, Hybrid meta-DFT, Reaction rate constant",

author = "Marwan Batiha and Mohammednoor Altarawneh and Abdullah Alsofi and Mohammad Al-Harahsheh and Ibrahem Altarawneh and Saleh Alrawadieh",

year = "2011",

month = aug,

doi = "10.1007/s00214-011-0940-x",

language = "English",

volume = "129",

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journal = "Theoretical Chemistry Accounts",

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T1 - Theoretical study on the reaction of hydrogen atoms with aniline

AU - Batiha, Marwan

AU - Altarawneh, Mohammednoor

AU - Alsofi, Abdullah

AU - Al-Harahsheh, Mohammad

AU - Altarawneh, Ibrahem

AU - Alrawadieh, Saleh

PY - 2011/8

Y1 - 2011/8

N2 - The reaction of aniline with hydrogen atom is investigated herein using the hybrid meta-DFT functional of BB1 K. Hydrogen atom is found to preferentially add at an ortho position. However, the fate of the o-(C6H5NH2)H adduct is found to be solely the deactivation of the initial addition channel. The rate constant for the abstraction channel (C6H5NH2 + H → C6H5NH + H2) is fitted by the expression 1.10 × 10-11 exp(-4,200/T) cm3 molecule-1 s-1. Our calculated rate constant for the abstraction channel agrees very well with the available experimental measurements. Satisfactory agreement is found between calculated and experimental measurements for the displacement channel (C6H5NH2 + H → C6H6 + NH2). Our detailed analysis for the corresponding displacements in toluene and phenol suggests that the three systems exhibit similar behavior with regard to the relative importance of abstraction and displacement channels.

AB - The reaction of aniline with hydrogen atom is investigated herein using the hybrid meta-DFT functional of BB1 K. Hydrogen atom is found to preferentially add at an ortho position. However, the fate of the o-(C6H5NH2)H adduct is found to be solely the deactivation of the initial addition channel. The rate constant for the abstraction channel (C6H5NH2 + H → C6H5NH + H2) is fitted by the expression 1.10 × 10-11 exp(-4,200/T) cm3 molecule-1 s-1. Our calculated rate constant for the abstraction channel agrees very well with the available experimental measurements. Satisfactory agreement is found between calculated and experimental measurements for the displacement channel (C6H5NH2 + H → C6H6 + NH2). Our detailed analysis for the corresponding displacements in toluene and phenol suggests that the three systems exhibit similar behavior with regard to the relative importance of abstraction and displacement channels.

KW - Abstraction vs. displacement

KW - Aniline

KW - H atoms

KW - Hybrid meta-DFT

KW - Reaction rate constant

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DO - 10.1007/s00214-011-0940-x

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EP - 832

JO - Theoretical Chemistry Accounts

JF - Theoretical Chemistry Accounts

IS - 6

ER -

Theoretical study on the reaction of hydrogen atoms with aniline

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Keywords

ASJC Scopus subject areas

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